


Fated Encounters

by GalahadThePure



Category: Fate/Grand Order, Fate/Zero, Pocket Monsters | Pokemon - All Media Types
Genre: Anal Fingering, Anal Sex, Crossover, First Dates, First Time, Fluff and Smut, M/M, Oral Sex, brief mentions of other ships
Language: English
Status: In-Progress
Published: 2019-03-07
Updated: 2019-03-07
Packaged: 2019-11-13 07:59:52
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 10,836
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18027839
Author URL: https://archiveofourown.org/users/GalahadThePure/pseuds/GalahadThePure
Summary: Iskandar is a simple Gym Leader in the Chaldeas region. When he has to go take his yearly progress exam with the Elite Four, he falls head over heels for one of its members, Lord El Melloi II. Immediately taken by love at first sight, Iskandar asks Lord El Melloi II out on a date! Lord El Melloi II decides to humor him, and says he'll go out with him if Iskandar can beat him in a Pokemon battle.





	1. Chapter 1

**Author's Note:**

> Hey guys, this is my first ever crossover fic! Both Fate and Pokemon mean a lot to me, so I figured a Pokemon AU would be great for my best boys. Plus, the fic that inspired me to start writing fanfiction was a Pokemon fanfic, MagmaKrystal's "Infamy." If you guys like Pokemon, particularly ORAS and Hardenshipping, I highly recommend checking it out!

     The small Ralts whimpered as three bratty youngsters kicked and stomped on it. Waver could only look on in horror as his poor Pokemon was tormented. He was heartbroken; he couldn’t even stand up for himself, let alone his only Pokemon.

   “Stop it!” Waver shouted, “Leave my Ralts alone!”

     He was greeted with a hefty punch to the gut, making him double over on the dusty path. This wasn’t fair… Pokemon battles were supposed to be a fun opportunity for trainers and Pokemon alike to get stronger, not one-sided beat downs.

     “Is Wavering Waver gonna cry?” one of the youngsters scoffed, “Don’t worry crybaby. Your Ralts is gonna be a great chewtoy for my Poochyena!”

     Waver wanted to cry. The physical pain of his bruises paired with the emotional duress of seeing his Ralts get abused were too much for him, but crying would only make things worse. He could only hope that they’d eventually get bored of picking on him so he could take his Ralts to the nearest Pokemon Center. Waver shrieked as one of his bullies pulled at his hair, forcing his head up to see his Ralts in its badly beaten state. A vicious Poochyena growled at the trembling, bleeding Ralts, readying to strike it with a sharp bite. Waver closed his eyes, preparing for the worst, but instead, he only heard the Poochyena yelp in shock. Hesitantly, he opened his eyes to see a Riolu tackling the Poochyena to the ground. Ralts hobbled over to his rightful owner, nuzzling up against him before returning to the safety of his pokeball.

   “Why don’t you guys pick on someone your own size!” an unfamiliar voice exclaimed.

     Standing before Waver was the owner of the Riolu who saved him and his Ralts from any further pain. He looked no older than Waver and his classmates, but none of them had ever seen him around the trainers’ school before. His messy red hair was pulled into a braid and his crimson eyes burned with passion against the sun-kissed skin of his face. Next to him stood a Mudbray who looked like he too was about to charge in on the fight, but held back out of respect for his owner. The youngsters were taken aback at the appearance of this stranger.

     “What do you think you’re doing?” one of the youngsters snapped, “This isn’t your fight! Scram!”

     “Pokemon battles aren’t excuses for bullying,” the red haired boy said, “I won’t stand idly by while you go overboard to hurt this trainer and his poor Pokemon.”

     “Tch, this guy’s Riolu is too strong. Come back Poochyena!”

     The Poochyena yipped as it returned to his pokeball.

     “You get off easy today Waver,” the youngster scoffed as he and his friends retreated.

     The red haired boy called back his Riolu and offered Waver a hand to help him to his feet.

     “Are you ok?” he smiled gently.

     Waver wiped the dust and tears from his eyes and grabbed his rescuer’s hand.

     “Y-yeah,” Waver sniffed.

     “Do you need a potion for your Ralts?” he asked, pulling a potion out of his bag, “It looked like he got pretty beat up.”

     “I-I was just gonna take him to the Pokemon Center. You don’t have to waste your potion.”

     “It’s no waste. I have plenty of them. At the very least, do you need someone to walk you to the Pokemon Center? It looks like you got pretty roughed up yourself.”

     “I-I’m fine… But… I guess I wouldn’t mind… for Ralts that is.”

     The boy grinned and grabbed onto his hand.

     “Then I’ll come with you,” he beamed, “Your name was Waver right?”

     Waver blushed, “Y-yeah… What’s your name?”

     The boy rubbed his chin in thought, “You know, you can just call me Rider. That’s what my friends call me!”

     This only made Waver’s blush deepen. His knight in shining armor was allowing him to call him by a nickname reserved for friends.

     “O-ok, Rider,” Waver stammered.

     “Would you mind telling me where the Center is?” Rider asked, “I’m just visiting the Chaldeas Region on holiday. I’m sure a local like you knows his way around better.”

     “Y-yeah. It’s right down the street.”

     “Alright! Come on Buschephalus!”

     Rider’s Mudbray whinnied and trotted alongside of the two. Waver’s heart fluttered as Rider gripped onto his hand.

     “You said you were just visiting right?” Waver asked, “Where are you from?”

     “I’m from Alola.” Rider replied, “It’s a small island region that doesn’t have a Pokemon League yet, but it’s a nice, relaxing place.”

     “How long are you here for?”

     “About a week. My parents are here on special business, but I like it here! I wouldn’t mind moving here when I grow up.”

     “Really?”

     “Yeah! I’ve always wanted to be a gym leader. The closest thing we have to that in Alola are Trial Captains and Kahunas, and not just any layperson can become one of them.”

     “You should! I mean… umm… I think you’d be a great gym leader…”

     Rider chuckled, “Thanks! I only have a few Pokemon right now, so I don’t know what type I’d specialize in yet, but I’d be happy with anything so long as Buschephalus is by my side. Do you have any Pokemon other than Ralts?”

     “Not yet,” Waver replied, “I might just try to become a professor. I don’t think I’d be a very good trainer, let alone a gym leader… Ralts is always getting hurt…”

     “Nonsense! I can tell your Ralts really cares about you. If you keep training him, I bet he’ll evolve to be super strong!”

     “You really think so?”

     “Of course! You’d be a great professor too, but don’t let some stupid bullies dictate your future for you! You can be whatever you want, Waver.”

     A flattered grin spread across Waver’s face.

     “Wow,” Rider gaped, “You’re really pretty when you smile.”

     “W-w-what?” Waver stammered embarrassedly, “You… you do know I’m a boy right?”

     “That doesn’t change the fact that you’re pretty!”

     Waver covered his face, completely flushed red with a mix of flattery and embarrassment.

     Rider giggled happily, “You’re so cute!”

     “Shut up!!!” Waver mumbled.

     Soon the two reached the Pokemon Center. Waver shuffled his feet and gripped harder at Rider’s hand.

     “U-umm…” he started, gathering all of his courage, “I-if you want, I can show you around more tomorrow… Only if you’re not busy…”

     Rider grinned ear-to-ear, “I’d love that! Shall we meet at the trainer’s school tomorrow then?”

     “Ok! Thank you again for helping me out today… It really meant a lot to me…”

     “No need to thank me. I just did what any decent person would do!”

     Rider waved goodbye as Waver walked into the Pokemon Center. He clutched the Pokeball holding Ralts to his chest. Maybe he really could become a great trainer someday.


	2. Chapter 2

     With one final attack, Iskandar’s Lucario fainted. Looks like the plucky trainer did it.

     “I suppose I still have more training to do myself!” he chuckled, “Good job kid! You’ve earned your Might Badge!”

     He pulled out a small pin shaped like a chariot and handed it to the young trainer.

     “You’ve bested my strongest fighting-type Pokemon,” Iskandar grinned, “Hold your head high as you continue your journey through the Chaldeas Region. Who knows, maybe you’ll be our next champion!”

     The young trainer nodded her head and rushed out of the gym, ready to tackle her next obstacles. Iskandar wiped the sweat from his brow and placed his pokeballs back in his bag.

     “I better heal these guys up before my next challenger approaches,” he said to himself.

   Iskandar walked past the ambitious fighting type trainers he had chosen to support him in his gym and out the door. As the Gym Leader for the bustling Pluriba City, Iskandar was tasked with testing trainers in the middle of their journey to the top. Fortunately for the rare occasions when he was defeated, his gym was located right next to the city’s Pokemon Center. He passed through the automatic doors of the Center and was greeted by the familiar music and call of the head nurse. Her long pink hair was tied back in a braided loop and she stood menacingly at the counter with her arms crossed.

     “Welcome,” the nurse said sternly, “Have you brought your Pokemon in for treatment?”

     “Good afternoon Florence,” Iskandar bellowed, “I suppose my team could use some help.”

     He handed his four pokeballs to Nurse Florence who laid them out to be healed. The machine behind her blinked several times, indicating that his Pokemons’ vitality had been completely restored.

     “Thank you for waiting,” she said, “Your team is fully healed.”

     “No, thank you Florence,” he replied, “It was so kind of you to offer me your position as the Pluriba City Gym Leader.”

     “Being both a nurse and a Gym Leader was quite the arduous task. I’m just happy that I was able to find a worthy replacement. Now I can practice medicine without worry.”

     Iskandar packed his Pokeballs away and began to leave the center, only to be stopped by the head nurse once again.

     “Wait,” she exclaimed, “Have you done your yearly progress exam for the Elite Four yet?”

     “Yearly progress exam?” he asked.

     “Pardon. I forgot you aren’t native to the Chaldeas region. At least once a year, Gym Leaders must fight the Elite Four to prove that they are strong enough to serve as a Gym Leader. Fortunately, the task isn’t that difficult. You only need to defeat two out of the four to maintain your position.”

     Since moving to the region five years ago, Iskandar had only heard rumors about the sheer strength of the Elite Four. Like Gym Leaders, they each specialized in one type of Pokemon. These particular four trainers stood out not only for their strength, but also for their strategy. The Mage of Flowers blessed by Fairies, Merlin, the Icy Shrine Maiden, Tamamo no Mae, the Queen of the Realm of Shadows and Darkness, Scathach Skadi, and the most versatile and infamous of them all, the Great Psychic Strategist, Lord El Melloi II. Even seasoned veterans struggled against El Melloi II’s strategy, and trainers across the land often said his Gallade could destroy even the strongest Dark types in one blow.

     “I recommend facing off against Tamamo and Skadi. You have the type advantage against their Ice and Dark teams as the Fighting type Gym Leader,” Florence suggested.

     “I’ll think about it,” Iskandar pondered, “I have always liked a challenge. When must I complete this exam?”

     “Sooner is preferable since you’re still relatively new as a Gym Leader, but you can take it any time so long as you do it before the end of the year.”

     “Well then, I supposed I’ll have to close the gym a bit early this Saturday. I’m sure trainers will understand if I’m off to face the Elite Four.”

     “I wish you the best of luck, Iskandar. Make sure your team is well prepared for the battle ahead.”

***

     Several days passed, and before Iskandar knew it, he was off to fight the Elite Four. As a Gym Leader, he was granted a pass through Victory Road, so he could head straight to the Pokemon League without unnecessary stalling from Veterans and Ace Trainers. The massive, chrome doors to the League opened before him. Unlike most instances where the Elite Four waited in their respective rooms, the four trainers were waiting for Iskandar in the main hall. Iskandar ascended the stairs, nervous but excited to meet the best trainers in the region. Upon greeting the four, Iskandar froze in place. The aura they gave off almost seemed otherworldly. They definitely embodied the term “Elite Four.” But it wasn’t the fox-like maiden, man who spawned flowers when he walked, or woman whose gaze could freeze hell over that caught his attention. Instead, his eyes went directly to the man in a black suit with long brown hair. While rather plain looking in comparison to the others, his emerald eyes glinted with pride and his pale skin seemed almost transparent. He was slender, but not sickly, and had an air of elegance about him. This was by far the most beautiful man Iskandar had ever seen.

     “Iskandar, leader of the Pluriba City Gym, I presume,” the man said.

     His voice was deep and smooth like honey, clouding Iskandar’s mind. Iskandar didn’t respond. It seemed to him as if no one else in the room mattered. He needed to make this man his.

     “Please,” Iskandar said, slowly approaching the man, “Go on a date with me!”

     The man seemed stunned. His brow twitched and blush spread across his cheeks.

     “Huh?” he peeped out.

     “HUHHHHH?” the other members of the Elite Four gasped.

     “You…” the man stuttered, “You surely must be joking…”

     “I’m not,” Iskandar replied, still lovestruck, “Please go out with me.”

     The room was silent for a few moments. Iskandar’s sincerity remained unwavering. The man before him attempted to respond, but only breath escaped past his twitching lips. Eventually the silence was broken by a feminine giggle.

     “You certainly have some balls, don’t you,” the woman in shrine maiden attire snickered, “To ask out the notorious Strategist of the Elite Four on a date.”

     Iskandar paused. This man was the strongest member of the Elite Four?

     “Shut up Tamamo…” he snapped, “I… I apologize for the rough start... Perhaps I should introduce myself. I am Lord El Melloi II; master of Psychic Type Pokemon. The shrine maiden over there is Tamamo no Mae, the man in the white robes is Merlin, and the woman in violet attire is Skadi. Now I assume you are here to take the progress exam, not just to make a fool of me and yourself.”

     “I am here for the exam,” Iskandar responded, “But I did not intend to embarrass you. You… you’re simply the most gorgeous man I have ever laid eyes on.”

     “I… umm… well,” Lord El Melloi II stammered nervously, “Now isn’t the time for flirtation. Honestly if you think you can pass the exam on flattery alone, you might be the biggest fool I’ve ever met.”

     “I might very well be a fool. I suppose love at first sight does that to you.”

     Lord El Melloi II’s face went completely red.

     “This one is smooth,” Merlin taunted, lifting his eyebrows suggestively, “He may not be the Prince Charming from your youth you’ve told us all about, but you might still…”

     “SHUT UP MERLIN!” he exclaimed, “I… I guess… Fine then… if you can beat me in a Pokemon battle, I’ll go out with you… Now… are you going to take your exam or not…”

     Iskandar humbly rubbed the back of his neck, “Oh yes. I apologize if I embarrassed you. Perhaps I’ll better convey my feelings in battle!”

***

     The doors to the Pluriba City Pokemon Center glided open. Dejectedly, Iskandar trudged in, dragging his bag of pokeballs and potions behind him.

    “Oh no Iskandar…” Florence fretted, “Is everything ok?”

     He didn’t reply, but simply plopped his Pokeballs on the desk in front of Florence. The color drained from her face.

     “Did you not pass?” she asked, concerned for Iskandar’s well being.

    “I passed…” Iskandar replied solemnly, “But I could only defeat three of them…”

     “Iskandar why are you sad? Three out of four is great! Especially when you only had to defeat two to pass.”

     Florence arranged his pokeballs on the healing machine and started it up. It dinged the familiar healing tune and revitalized his Pokemon.

     “I couldn’t beat him…” Iskandar moped.

     “Him?” Florence asked, returning the pokeballs to their rightful owner.

     “The Psychic Type member…”

     “But that’s understandable. You went in with your best team of fighting types. They’re naturally weak to psychic types. You don’t need to be upset over that.”

     “Florence, the exam isn’t what I’m upset about.”

     Not skipping a single detail, Iskandar informed Nightingale of how he fell head over heels for Lord El Melloi II.

     “No one ever mentioned how beautiful he was,” Iskandar complained, “To think I had a chance to make him mine… It’s frustrating seeing him slip from my grasp like sand through my fingers…”

   He was greeted with a sharp slap to his cheek. Florence furrowed her brow and shook her head.

     “To think I handed my gym down to a pathetic excuse of a man who would give up after one attempt,” she scolded, “I’m disappointed in you. I thought you were the kind who would pursue his dreams until they became a reality.”

     “What do you mean?” he winced, rubbing the reddening mark on his cheek.

     “He simply said you had to defeat him in battle. He never said you couldn’t make multiple attempts. If you truly care for this man, keep on trying. The Iskandar I passed my gym onto would do so.”

     Iskandar’s eyes lit up with a new conviction.

     “You’re right,” Iskandar replied, “I can’t give up. Dreams are meant to be chased. I’ll keep pursuing this trial until I emerge victorious!”

     Florence smirked, “That’s the man I know. If you wish to close the gym early so you can challenge him more frequently, I’ll gladly fill your place in the gym for the time being.”

     “Thank you Florence. I owe you.”

   “Think nothing of it. You’re not the only one who will emerge stronger from this trial. This is an excellent opportunity for your team of Pokemon to overcome their weaknesses as well.”

     With renewed determination, Iskandar grabbed his pokeballs and returned to his home, ready to train his Pokemon until both he and his team were worthy enough to face the Psychic paragon of the Elite Four.


	3. Chapter 3

     Lord El Melloi II slammed his empty glass onto the bar counter in the Elite Four lounge.

     “He’s not giving up at all!” he exclaimed, “How many days in a row has it been? Most people would have given up by now, or at the very least went back to train their Pokemon until they surpass mine.”

     Tamamo giggled as she sipped at her hot sake, “He must really like you. I’m surprised you haven’t just given in and gone out with him yet.”

     “Sometimes determination can be a bad thing you know…” he worred, “What if this man is a stalker…”

     “Normally I’d agree with you,” Skadi interjected, twirling her half full glass of wine in her hand, “But something tells me this is fate trying to finally get you a boyfriend. It works in funny ways. I never would have thought I’d be dating the Pokemon Contest Queen Medb, but she’s turned out to be the ideal partner for me.”

     “I already found my ideal partner a long time ago…” El Melloi II reminisced.

     “Is this about that Alolan boy you met when you were younger?” Skadi groaned, “Waver, you do realize that Alola has its own Pokemon League now, right? It’s been 20 years. He might very well be a Gym Leader over there now.”

   “Besides, I wouldn’t look a gift Rapidash in the mouth,” Tamamo added, “That Iskandar guy is pretty hot, and I know you have a thing for redheads.”

     “I’d be lying if I said I didn’t think he was attractive,” Waver responded, “Hell, he’s just my type… I just feel like I’d be betraying _him_ …”

     “I have half a mind to sabotage your team the next time Iskandar comes to challenge you,” Merlin teased, “He doesn’t have the exam pass anymore. He had to fight his way through Victory Road to come challenge you. Waver, you can’t just shut yourself off to everyone who shows interest in you just because some kid stood up for you when you were younger.”

     “He didn’t just stand up for me…” Waver insisted, “He changed the course of my life… I probably would have released my Ralts and given up on being a trainer if he didn’t rescue me… Call me a sentimental old fool who can’t get over his first crush, but if there’s a chance that I could see him again; maybe even be his partner, I’d gladly take it…”

     “Ok but what if, and this might totally blow your mind, Iskandar _is_ that kid,” Tamamo suggested.

     “Impossible,” Waver denied, “ _Rider_ was my knight in shining armor. I doubt he’d grow up to be a muscle-headed brute who lacks any subtlety…”

     “A muscle-headed brute who’s a _Gym Leader_ with _red hair, red eyes_ , and _tan skin_ ,” Merlin said, “Didn’t you say Rider was just that kid’s nickname anyways?”

     Waver stood up from his seat, “I’m going outside to get some fresh air.”

     He stormed out of the lounge, into the lobby, and through the gates of the Pokemon League. The night air sent a chill up his spine, but it helped to cool his head. Ever since he met Rider as a kid, Waver tried to better himself as a trainer and as a person. Whether it was inheriting the title of Lord El Melloi II from teaching at the Pokemon Trainer’s Association in Londres Town to eventually becoming a member of the Elite Four, Waver wanted to live up to the potential Rider saw in him. Still, Merlin’s and Tamamo’s words stuck with him. What if Iskandar, the Gym Leader who wouldn’t give up on the idea of dating him, _was_ his Prince Charming? He shook his head.

     “No, there’s no way that brute can be him,” Waver assured himself, “Rider’s favorite Pokemon was his Mudbray… well… probably Mudsdale now, and Iskandar only uses fighting types… He… he can’t be…”

     Suddenly, Waver felt a hand on his shoulder and was brought back to reality. Standing in front of him was Iskandar, apparently ready to go for another rematch.

     “Do you have any idea how late it is?” Waver scolded.

     “I’m sorry if it’s an inconvenience,” Iskandar said, bowing his head in respect, “I just thought of a new strategy I wanted to try.”

     “At least it’s something different. Honestly, do you even expect to win against a Psychic type trainer using only Fighting types?”

     “That’s why I brought a non-Fighting type tonight to battle. He’s more like a friend to me, but he’s the strongest Pokemon I have.”

     “You’re really not going to give up until I concede to go on a date with you, are you…”

     “While that is definitely a big reason why I keep coming back, I actually just really want to see if I can beat you. You’re a really talented trainer who loves his Pokemon. Both my team and myself have started to enjoy battling you.”

     Waver blushed, “Well at least you’re changing things up a bit. Now, lets get this over with…”

     He guided Iskandar back into the lobby of the Pokemon League and opened the door to his chamber. A beam shot down from the ceiling, transporting the two to the battle stage. Given Iskandar’s “glass cannon” strategy he had used in previous battles, Waver thought bringing out his signature Gallade wouldn’t even be necessary this battle.

     He began by throwing out his Espeon, probably his weakest Pokemon in his team, but still strong enough to fend off fighting types. Iskandar responded by unleashing his Pangoro into the frey. It appeared his strategy had slightly changed. He must have been getting serious by adding a dual fighting/dark type to his lineup.

     “Pangoro! Use dark pulse,” Iskandar shouted.

     The Pangoro stared at the Espeon menacingly before launching a dark aura forward. Not only did it deal over half of Espeon’s health, the move also made it flinch. Waver was oddly impressed. The Pangoro attacked once again, finishing off the Espeon and making it retreat back to its pokeball. It looked like Waver couldn’t take him so lightly this time. He called out the next member of his team, his formidable Metagross. Not only was this Pokemon one of Waver’s heaviest hitters, it also had a higher speed stat, allowing it to move before Iskandar’s Pangoro.

     “Metagross, use Aerial Ace!” he ordered, “Don’t think you’re the only one who uses TMs!

     The steel/psychic type Pokemon flew forward, slashing at the Pangoro. Iskandar’s heart nearly stopped as his Pokemon tanked the super effective move. Fortunately for him, it survived with one hit point, thanks to its strong bond with its trainer. Iskandar smirked shrewdly.

     “Use Payback,” he commanded.

     Waver’s jaw dropped as the Pangoro unleashed a surge of energy, reflecting his Metagross’ damage and taking it out in one hit.

     _“Calm down, Waver,”_ he thought to himself, _“You’ve still got two Pokemon left, plus one of them is your Ace in the Hole… You can do this.”_

     Waver called out his next Pokemon, Musharna. Thanks to his meticulous breeding and patient training, this Musharna was the tank of his lineup.

     “Musharna,” he yelled, “Use Dazzling Gleam!”

     With a flash of light, Iskandar’s Pangoro fainted, retreating to its Pokeball. Sweat began to drip down Iskandar’s forehead as he threw out his next Pokemon, a Mienshao.

     _“Just as I thought, he is an idiot,”_ Waver thought, _“Throwing out his secret weapon first… My Musharna has destroyed the rest of his team plenty of times before. The rest of this battle should be a piece of cake.”_

Waver’s Musharna continuously fired off Dazzling Gleams and Psybeams, taking out Iskandar’s team one by one. Soon enough, Iskandar was down to his last Pokeball.

     “Looks like I gotta use my secret weapon,” he grinned.

     _“What?”_ Waver froze, _“His secret weapon wasn’t the Pangoro?”_

     “GO BUSCHEPHALUS!” Iskandar yelled as he threw out his last pokeball.

     To Waver’s surprise, the Pokemon that materialized was not a fighting type at all, but a large, powerful Mudsdale. He was stunned. Waver had heard that name before. It was the very same name of Rider’s Mudbray, all those years ago.

     “After battling with you so many times, I know your team was built to specifically counter fighting and dark types,” Iskandar smirked, “But not even your Gallade knows a move that counters a _ground_ type Pokemon!”

     _“This has to be a coincidence,”_ Waver fumed, _“I’m sure that Mudsdale isn’t Rider’s Mudbray… It can’t be…”_

   Waver scowled and gripped at Musharna’s pokeball.

     “I like that look in your eyes,” Iskandar remarked, “It’s like you’re finally taking me seriously. NOW LET’S GO, BUSCHEPHALUS!!!”

     Buschephalus and Musharna hurled attacks at each other left and right. Due to both of their impeccably high defenses, the battle between these two particular Pokemon felt like it lasted a lifetime. After exhausting all of Buschephalus’ “High Horsepowers,” Waver’s Musharna finally fainted. He began to laugh victoriously.

     “I’m sorry Iskandar, but it looks like this battle is over,” Waver cackled, “Your Mudsdale is a few attacks away from fainting, but my strongest Pokemon is full of life and itching for a fight. NOW GO! GALLADE!”

     Waver’s final, strongest Pokemon, his notorious Gallade, emerged from its pokeball. But to Waver’s absolute shock, it appeared to have no interest in fighting this Mudsdale. On the contrary, it chirped as if it was happy to see it; almost as if… it recognized it from a long time ago.

   “G-gallade?” Waver stammered, losing his composure, “W-what are you doing? Why aren’t you finishing that Mudsdale off?”

     Iskandar’s Mudsdale too seemed affected by the impasse, as it whinnied happily at the sight of Waver’s Gallade. Waver dropped to his knees in defeat. Tears started to spill from his eyes. There was no denying it at this point. Even his Gallade could tell. This man, who Waver had been trying so hard to dissuade from pursuing him, was the very same man he harbored feelings of love and admiration for since his childhood.

     “R-Rider…” he sobbed softly.

     “Well, strange as it is, it seems like our Pokemon refuse to fight each other,” Iskandar said cluelessly, “I suppose we’ll have to call this one a draw… I was really close this time, but I’m still going to keep trying! I know if I keep it up then someday…”

     “I concede…”

     “Wait a minute… What did you just say?”

     Waver called his Gallade back to its pokeball and wiped the tears from his eyes, “I concede defeat. You’ve beaten me…”

     “Wait, REALLY?” Iskandar beamed, “I won? So then, does that mean…”

     “I expect you’ll take me somewhere nice,” Waver smiled, “Let’s say, Friday at 7 PM?”

     “So you’ll actually go out with me?”

     “I won’t go back on what I said. I look forward to our date.”

     Waver pulled out a piece of paper and a pen and scribbled down his phone number before placing it in Iskandar’s hand.

     “Call me later, ok?” Waver flushed.

     Before Iskandar could say anything, Waver had run to the teleporter and out of the chamber. He looked down to the sheet of paper and smiled.

     “I won’t let you down,” he beamed.


	4. Chapter 4

     Iskandar slicked his messy, red hair back, taming it into a stylish coif. He trimmed his beard and sprayed a small spritz of cologne around his neck before buttoning up his shirt and tying his tie. As someone whose style typically consisted of t-shirts, jeans, and work out clothes, wearing a suit felt alien. He hoped that at least his date would like it. Iskandar grabbed his pokeballs, wallet, phone, and keys and headed for the door. Buschephalus whinnied at him as soon as he stepped outside and began to lock the door.

     “I’ll be back later boy,” Iskandar smiled, petting his Mudsdale on the snout, “Hold down the fort for me while I’m gone.”

     Buschephalus hung his head sadly. His eyes glinted like a sad Poochyena. Iskandar shook his head.

     “Ok boy, you can come,” he conceded, “But you’ve got to stay in your pokeball.”

     Buschephalus neighed happily. Iskandar pulled out Buschephalus’ pokeball and called him in before calling out his Hawlucha and ordering it to use Fly. The Hawlucha somehow managed to pick Iskandar up, and ascended into the sky, flying them towards Londres Town. It was times like this when Iskandar missed the Ride Pokemon system employed in Alola. Eventually he arrived at his destination. Fortunately, he was fifteen minutes early, allowing him to stop by the nearest florist and pick up some roses for his date.

***

     Waver heard a knock on the door to his flat. He opened the door to see Iskandar, wearing a black suit and holding a bouquet of red roses.

     “Wow,” Waver said, “You clean up nicely.”

     Iskandar rubbed the back of his neck and smiled as he handed Waver the flowers.

     “And you look amazing as well, Lord El Melloi,” he flirted.

     “I have a first name you know,” Waver replied, “Honestly, were you planning on calling me that all night?”

     “I didn’t know when it would be appropriate to ask. What should I call you?”

     “Waver.”

     Iskandar rubbed his chin, “Waver, hm? That’s an interesting name. Is it common in this region?”

     Waver froze. Did Iskandar seriously not remember? Was he really this much of an idiot, or did Waver not leave that much of an impact on his life… To be fair, it was twenty years ago, but it still hurt a bit.

     “It’s…” he sighed, “Not particularly common…”

     “Really?” Iskandar replied, “I feel like I’ve heard it before… Well, shall we head out?”

     “Let me just put these flowers in a vase. Thank you for them by the way.”

     “I’m glad you like them.”

     Waver filled a vase with some cold water before placing the bouquet of flowers in. He turned around to see Iskandar smiling and holding out his hand, waiting for him. Waver shook his head. Even if the “Rider” from his childhood had forgotten about him, it was clear that Iskandar definitely cared about him.

     “So,” Waver began, “Where are we going tonight? Will I need to bring a flying type?”

     “No need,” Iskandar grinned, “The restaurant is right here in Londres Town. I’m sure you’ve heard of Chef Emiya.”

     “Chef Emiya? He runs the nicest restaurant in town!”

     “Well, I was able to get a reservation at his place, Unlimited Steak Works!”

     “It’s always booked out months in advance. Even as a member of the Elite Four I’ve never been able to get a reservation. How did you manage to get one?”

     “I have my connections.”

     “Do you want to go dutch? I heard that place is pretty expensive…”

     “Don’t worry about it. This date is my treat.”

     Iskandar extended his hand and smiled, “Now, shall we?”

     Waver took his hand. Iskandar pulled it up to his mouth and kissed him on the knuckles, making a flustered blush creep across Waver’s face. The two headed to the door and Waver pulled out his keys to lock up his flat. Iskandar guided his date out of the lobby of the apartment complex and into the lively streets of Londres. Unlimited Steak Works was located near the Clocktower, so the distance was easily walkable. The frigid air around them prompted Waver to grip Iskandar’s hand tighter and huddle closer for warmth. Streetlights illuminated the grey sidewalk and awnings from nearby storefronts cast shadows upon them. The moon had just started to peak out from the bed of fog and clouds over the city and small stars twinkled in the inky blackness of the night sky. Businessmen and women were returning from their long day of work, retreating into the depths of the tube stations to return to the warmth of their homes and families. As the lights of the skyscrapers dimmed, fluorescent lights of bars and restaurants brightened, transitioning into the elegant but lively nightlife of Londres. They soon reached the Clocktower. Its face glowed a faint yellow as the black clock hands ticked along. Next to the tower sat the Pokemon Academy, where young adults would flock to study the nature of Pokemon and the world around them. This area was quite nostalgic to Waver, as he used to teach here before he became a member of the Elite Four. They passed by the campus, making their way to the stylish bistro down the street. A twisting line formed outside of the door and on the awning in cursive read “Unlimited Steak Works.”

     “Is this the queue to get in?” Waver gaped.

     “Only if you don’t have a reservation,” Iskandar chuckled proudly, “Don’t worry, just follow me.”

     Iskandar lead Waver up to the hostess. Her long, violet hair was tied to the side in a pink ribbon.

     “Welcome to Unlimited Steak Works!” she smiled, “Do you have a reservation with us tonight?”

     “Yes,” Iskandar responded, “It’s under ‘Iskandar’ party of two.”

     The young woman gasped, “Sir! We’ve been waiting for you! It’s an honor for you to eat at our humble establishment! Please follow me. We have a VIP table reserved for you.”

     She pulled out two menus before bowing and guiding the two to a fancy booth in the center of the restaurant. The cloth napkins were folded to resemble Swannas and the plates and cutlery were the finest porcelain and sterling silver.

     “Your server will be with you shortly,” she smiled.

     The hostess then returned to her position at the podium near the front of the restaurant.

     “VIP huh?” Waver asked, “Do you know the chef?”

     “I suppose you can say that,” Iskandar responded, “I’m originally from Alola and my family owns a restaurant over there called the Battle Buffet. Chef Emiya trained as both a chef and a Pokemon trainer under my parents, so he always is willing to set aside a table in case my family or myself wants to eat at his restaurant.”

     “Wow, I never would have guessed you came from a family of restaurateurs. I’ve always wanted to visit Alola. A childhood friend of mine lived there.”

     “It’s a beautiful region. I miss it from time to time, but I always wanted to be a gym leader. If I had stayed there, I probably would have just taken over the family business, but I’m happy that I moved here. I have my dream job, made plenty of friends, and most importantly, got to meet you.”

     Waver blushed. Before they could continue the conversation, their waitress came to their table. She placed down two glasses of water and pulled a pen out of her apron.

     “Welcome to Unlimited Steak Works,” she said cheerfully, “My name is Artoria and I’ll be your waitress tonight. Have you ever dined here before?”

     “I have, but it’s his first time here,” Iskandar responded.

     “Well our menu is comprised of two different options. One is your standard, a la carte menu, and the other is a four-course prix fixe of some of Chef Emiya’s finest dishes. I highly recommend his Wasabi Mayo Magikarp or Herb Butter Miltank Filet Mignon. Both of those are included in the prix fixe as well. Do you two need a minute to decide?”

     Waver looked down at his menu. His eyes bulged when he saw the price of an appetizer, let alone the prix fixe menu.

     “Does the prix fixe sound good to you Waver?” Iskandar asked.

     “I mean, it does,” Waver answered guiltily, “But it’s a lot of money… Are you sure you don’t want to go dutch?”

     “The price doesn’t matter. Tonight is about us sharing each other’s company and enjoying delicious food. We’ll take the prix fixe menu tonight.”

     Artoria jotted down the order on her notepad and took their menus.

     “The prix fixe comes with wine,” she said, “Would you prefer red, white, or sparkling?”

     “I’ll have a cabernet,” Iskandar replied.

     “I’ll take the same,” Waver added.

     “I’ll have your wine and bread out in a bit,” she said, turning on her heel to head to the kitchen.

     Once she had left, Waver was determined to get the “Rider” from his childhood remember him.

     “So,” he continued, “You said you were originally from Alola? Why did you choose to move to Chaldeas? Plenty of other regions have Gyms and Pokemon Leagues.”

     “Well,” Iskandar responded, “My family and I travelled a lot when I was younger; trying to make business connections you know; and I liked Chaldeas the best. There was so much variety here and the locals certainly gave me a warm welcome. I can’t remember his name, but there was a cute kid who was my basically my best friend for the week he was here. I wonder what he’s up to nowadays…”

     _“He’s having dinner with you! Idiot!”_ Waver thought to himself.

     “Bah, sorry for talking so much about myself,” Iskandar apologized, “Tell me about yourself, Waver.”

     Waver perked up, “Well, before I was in the Elite Four, I worked as a Professor for the Pokemon Academy at the Clocktower. Being a trainer was initially more of a side thing for me. But my little sister Reines kept on bragging to the higher ups about how strong my Gallade was. That eventually caught the attention of the new Champion, Romani. Since the old Psychic Type Elite Four member had retired, Romani decided to recruit me.”

     “I didn’t know you had a sister.”

     “Adoptive, but she’s still my sister nonetheless. That’s why I took the title of Lord El Melloi instead of my own surname when I became a professor. It’s granted to the eldest child of my adoptive family. Normally it would have gone to Reines after her uncle Kayneth passed away, but she wasn’t ready to take over the family, so she gave the title to me instead.”

     Artoria returned with a basket of bread, two fresh, Rindo salads, and a bottle of wine. She placed the bread at the center of the table, set the plates of salad in front of the two, and poured their glasses of wine.

     “Your appetizers will be out shortly,” she said, “Let me know if you need anything.”

     As soon as she returned to the kitchen, Iskandar was eager to learn more about his date.

   “Have you always lived in Chaldeas?” he asked

     “I was born and raised in Londres,” Waver replied, “I did go to Training School in Fuyuki Village though.”

     “That’s where I visited when I came here! You’re so good with Pokemon, I bet you were a top student.”

     “On paper, yes. But I only had one Pokemon at the time, and he and I always got picked on by other kids.”

     “Did the teachers ever do anything about it?”

     “If they caught it… Otherwise, Ralts and I had to fend for ourselves.”

     Iskandar paused. Waver could practically see the gears turning in his head.

     “Ralts…” he repeated, “Your first pokemon was a Ralts?”

     “He’s my Gallade now,” Waver replied, “But when I was nine, he was just a weak little Ralts. I almost let him go actually.”

     “Why?”

     “Because we were constantly getting beaten up, but thanks to a chance encounter, I decided to keep on training him. Now he’s my strongest pokemon, and it’s all thanks to you, Rider.”

     Iskandar’s jaw dropped.

     “That… That kid I met those twenty years ago… The one with the Ralts who was being bullied… That was you?” Iskandar realized.

     “Yeah, that was me,” Waver smiled, “I’m sorry I made you go through so much to get me to go out with you. I had no idea that the savior from my childhood was trying to court me.”

     “And I had no idea that the cute kid that showed me around Fuyuki Village was you. You’ve certainly aged well.”

     “You flatter me. Besides, I wasn’t that cute of a kid. I was just a scrawny little nerd.”

    “With a smile that could light up a room. I’m sorry I forgot your name, but I had a blast hanging out with you for a week.”

     Waver blushed, “I did too. I’ll be honest, I was really sad when you left. I was always hoping that you’d move to Chaldeas. You were… kind of my first crush.”

     Iskandar nearly spat out his wine.

     “So you’re saying,” he said, “You liked _me_?”

     “I did, and I still do,” Waver flushed.

     “So then I guess our feelings are mutual,” Iskandar smirked, stretching out his hand to hold onto Waver’s.

     Waver clasped his hand tightly, “Yeah, I guess so.”

     The rest of the dinner was spent catching up, laughing, and of course eating Chef Emiya’s delicious food. Tender Milktank steak, flaky, fresh Magikarp, succulent Mareep chops; every plate of the course was delectable. As their waitress brought their dessert out, a man with tan skin and white hair came along with her. He was wearing a white chef’s smock with a few small stains on it.

     “I hope the meal was to your liking,” he said.

     “Delicious as always, Shiro,” Iskandar responded, “By the way, this is my date for tonight. Waver, meet Chef Emiya Shiro.”

     Waver gasped, “Chef Emiya, it’s an honor to meet you. Your food is superb!”

     Emiya chuckled, “I’m glad you enjoyed it. It’s a pleasure to serve an old friend and a member of the Elite Four.”

     “Thank you again for saving us the VIP table,” Iskandar grinned, “I’ll have to tell my old man to give you and your wife the VIP treatment as well the next time you’re in Alola.”

     “I’m sure Rin will certainly appreciate that,” he replied, “By the way, I have a special dessert for you and your date.”

     Chef Emiya placed a white box down on the table. Inside were several, colorful sandwich cookies.

     “Fresh Pokemacarons,” he explained, “They’re a delicious dessert from Kalos for humans and pokemon alike. These ones are on the house.”

     “Oh, thank you,” Waver said.

     Artoria placed the check in front of Iskandar and grinned.

     “Here’s the check for whenever you’re ready,” she smiled.

     Iskandar opened the bill and slid his card in before handing it back to their waitress. Waver was amazed he could do so without wincing. Being a gym leader wasn’t exactly the best paying job in the world. How rich was he that he could afford this kind of meal? Artoria soon after returned with the check. Iskandar signed it, left a well-deserved tip, and set the bill down on the table. He stood up, grabbed the box of pokemacarons, and offered his hand to Waver.

     “Did you enjoy your meal?” he asked.

     Waver took his hand and stood up, “It was excellent. Thank you Iskandar.”

     A gentle smile spread across Iskandar’s face and his eyes lit up.

     “I’m glad,” he whispered.

     His grip on Waver’s hand slightly tightened as Iskandar guided him out of the bistro. Outside, rain poured down from the cloudy skies of Londres. Large puddles had formed along the black asphalt of the streets and wind whipped heavy drops against their skin.

     “It’s pouring,” Iskandar commented, “Maybe I should have brought an umbrella.”

     “I should have warned you,” Waver regretted, “It rains all the bloody time in Londres…”

     “Do you want me to call a cab to get you back to your flat?”

     “I’m fine with walking back… But you weren’t planning on flying home in this weather, were you?”

     Iskandar rubbed his chin, “I wasn’t expecting rain, but I think my Hawlucha can manage.”

     “You… Would you like to come back to my place?” Waver offered nervously, “I don’t want you risking your health flying back in the middle of a downpour.”

     Iskandar raised an eyebrow and grinned cheekily. Waver blushed as Iskandar closed his eyes and tilted his chin upwards, leaning in close to him. He felt Iskandar’s chapped lips press lightly against his supple ones, chastely kissing him before pulling away.

     “I’ll gladly take you up on that offer,” he accepted.


	5. Chapter 5

**Notes for the Chapter:**

> Its smut time

     Waver opened the door to his flat and hung his and Iskandar’s sopping wet coats on his coatrack. Perhaps walking home in the pouring rain wasn’t the best idea. The two of them were completely soaked.

     “I’ll go grab some towels,” Waver said apologetically, “Make yourself at home.”

     Iskandar took off his flooded shoes, set the box of pokemacarons on the counter, and made his way into the living room. Its décor was minimalistic, save for a few photos in frames, a bookshelf, and a video game console hooked up to the television. Iskandar never would have guessed that a serious guy like Waver was into video games, but it wasn’t necessarily a bad thing. After all, Iskandar loved video games too. Waver soon returned with several towels in his hands. His long, wet, brown hair was tied back into a ponytail and he had changed into some dry slacks and a black, long sleeved shirt. He handed Iskandar a towel and walked into the kitchen.

     “Want me to put on a kettle of tea?” Waver asked.

     “That sounds good,” Iskandar responded, “I’ll just take whatever you’re having.”

     Waver grabbed a kettle from his cabinet, filled it with water, and set it on his stove to boil. He felt a strong pair of arms wrap around him from behind and a bearded chin nestle on his shoulder. Waver turned his head slightly and was greeted with a kiss on the lips. It was longer and more passionate than their first, lingering on Waver’s lips even after Iskandar pulled away. Yet Waver dove back in, craving more. His lips parted, allowing Iskandar to slide his tongue inside of his mouth. Waver mewled as Iskandar’s wet tongue explored his palate, intertwining with his own. Breathlessly, he pulled away, leaving a string of saliva still connecting their gaping lips.

     “Want to…” Waver panted, “Move to the couch?”

     Waver yelped as Iskandar picked him up like a rag doll, carrying him to the couch. He sat down on the soft cushions and positioned Waver in a straddle over his lap. Before Waver could say anything else, Iskandar had pulled him in close for another kiss. He ran his fingers through Waver’s wet hair, massaging his scalp while forcing his tongue past Waver’s pliant lips. Waver swung his arms over Iskandar’s shoulders, graciously accepting the kiss. Iskandar’s hands wandered from the silken strands of Waver’s hair, down the slender slope of his back, landing as the curve of his ass. He gently groped at the soft cheek, making Waver’s breath hitch. This was bad. Waver could feel himself starting to get hard, and Iskandar was clearly aroused as well. Skadi’s words of advice suddenly popped into his head.

     _“It’s important to set boundaries,” she warned, “If you jump straight into sex on the first date, he might think you’re easy and it could turn into a one night stand.”_

     Before they could go any further, Waver pushed himself away.

     “Was that too much?” Iskandar worried.

     “N-no, it’s just...” Waver replied, trying to think of an excuse, “Your clothes… you should take them off…”

     “Oh?” Iskandar growled, squeezing Waver’s ass harder.

     “No, I mean…” he whimpered, “You’re soaking wet. If you stay in them, you’ll catch a cold… I can throw them in the dryer for you if you want.”

     “Is that so? Well, I suppose I can’t argue with that. Mind if I use your shower while my clothes dry?”

     “Sure… It’s right down the hall, next to my bedroom.”

     Waver crawled off of Iskandar’s lap and guided him to his room.

     “You can just leave your clothes outside the bathroom door,” Waver said.

     Iskandar kissed him on the forehead, “Ok then. I’ll make it quick.”

     He walked into the bathroom and closed the door behind him. Waver sat down on his bed and pressed his palms to his face. He could practically hear Skadi and Merlin’s advice for his date running through his head like a shoulder angel and devil.

     _“There’s nothing wrong with going all the way on your first date_ , _”_ Merlin’s voice echoed, _“If you want it, go for it!”_

 _“Considering this advice is coming from a promiscuous incubus like Merlin, I don’t think it would be wise of you to take it_ ,” Skadi’s words reverberated in his mind, almost as if the two were arguing, _“How will you know if this man really respects you if you spread your legs on your first date? You could just be another conquest in his eyes!”_

_“Don’t let this salty hag shame you for following your desires. If he thought of you as a sexual conquest, he wouldn’t have tried so hard in courting you. Follow your heart, but more importantly, follow your dick!”_

_“This vulgarity is the exact reason why you should heed my warning and wait! At least abstain until the third date!”_

_“I pity poor Medb… Dating a prude must be so unsatisfying.”_

_“Leave my girlfriend out of this!”_

     “Can you two just shut up?!” Waver shouted.

     He slapped his hands over his mouth, realizing that he said that out loud. Iskandar poked his head out from behind the door with his clothes piled up in his hand.

     “You alright out there?” he asked.

     “I’m fine,” Waver blushed, taking his wet clothes, “I’ll go throw these in the dryer…”

     Iskandar closed the door once again and Waver heard the sound of running water from the showerhead behind it. He headed to the drying machine, loaded up the wet clothes, and started the machine up. The kettle on the stove started screaming and spewing steam. He rushed over to switch it off before the water boiled over. It looked like they’d probably pass on tea tonight. Waver sighed melancholically. He feared he was overthinking this whole thing. Truth be told, he had always dreamed of “Rider” making love to him since his teenage years. Unfortunately, this caused him to remain a virgin, even at 29 years of age. But Iskandar didn’t know that. He didn’t know what to do. Should he follow Skadi’s advice and hold off on sex, or give into his desires like Merlin suggested? It seemed like a loss either way. He didn’t want Iskandar to think he was a slut, but he feared Iskandar wouldn’t want to go out with a prude either… He returned to his room and heard the water shut off. Waver’s jaw dropped as soon as the door to the bathroom opened. Iskandar was wearing nothing but a towel around his hips. Beads of water dripped off of his tight musculature and steam rose from his olive skin. A few scars riddled his body and a line of red hair trailed up from his groin. Waver was in awe.

     “Oh? Do you like what you see?” Iskandar grinned.

     Waver couldn’t speak. His desires had completely taken control of him. He needed Iskandar, and he needed him now. Waver threw his arms over Iskandar’s shoulders and pulled him into a deep kiss. Iskandar happily returned the kiss, settling his arms around Waver’s waist to get closer. Without breaking the kiss, they began moving to the bed. Before Waver could realize what was going on, he was being pressed into the sheets of his bed with Iskandar lying on top of him. He could feel Iskandar’s erect member tenting under the towel and grinding against his thigh. Waver pulled away for a moment, flustered and nervous.

     “Did I make you uncomfortable?” Iskandar worried, “We can stop if you want.”

     “It’s not that,” Waver replied earnestly, “I don’t want to stop. Hell I wouldn’t mind going even further… I’m just a little scared…”

     “Why is that?”

     “I… I don’t want you to think I’m rushing things… Skadi told me that it’s distasteful to have sex on your first date; that it’s a recipe for one night stands, not relationships…”

     “I get it… So what you’re saying is, you want a relationship?”

     Waver’s face went bright red. He stammered and mumbled before finally gathering his courage.

     “…Yes…” he said, “Iskandar, I like you. I like you a lot. I want you to be my boyfriend.”

     Iskandar closed his eyes contently. A gentle smile spread across his face.

     “That makes me so happy,” he replied, “I’d love to, no, I’d be honored to be your boyfriend, Waver.”

     Tears of joy leaked from Waver’s eyes. Rider, or rather Iskandar, the hero from his childhood, was now his partner.

     “Don’t cry,” Iskandar said, wiping off Waver’s tears, “Are you not happy?”

     “I’m overjoyed,” Waver sniffed, “to be boyfriends with the man of my dreams.”

     “You’re so cute. It seems I’ve truly found a wonderful partner as well.”

     Before Waver could retort, Iskandar’s lips were on his, kissing him passionately. His hands wandered up under the fabric of Waver’s shirt, caressing the soft skin of his stomach before moving to his chest. Waver squeaked as Iskandar’s thumb rubbed over his hardening nipple.

     “Did you like that?” Iskandar growled.

     “Mmm… mhm…” Waver mumbled.

     Iskandar smirked as he slid Waver’s shirt off, throwing it to the floor. His fingers hooked around the waistline of Waver’s pants, making Waver fidget.

     “May I?” Iskandar asked.

     “Go ahead,” Waver responded nervously.

     Iskandar slid his fingers under Waver’s slacks, undoing the button and unzipping them before tugging them off his legs. His erection was straining against his boxer briefs and a small, wet spot had formed by the tip of his dick. Iskandar licked his lips as he removed the last layer of clothing from his lover’s body, leaving Waver completely bare beneath him.

     “You’re beautiful,” Iskandar whispered.

     Waver yelped as Iskandar’s hand curled around his erect penis, slowly stroking him. He kissed at the insides of Waver’s thighs, nibbling on the sensitive flesh and trailing his tongue across his soft skin.

     “I-Iskan…dar…” Waver panted.

     “Does it feel good?” Iskandar cooed.

     “It does… but… I want to touch you too…”

     Iskandar released the grip on Waver’s member and kissed him on the tip of his nose.

     “As you wish,” he said.

     He removed the towel from around his waist, letting it fall to the floor. The sight made Waver swallow hard. Iskandar’s cock was HUGE. He was hung like a Mudsdale! It had to be over a foot long, and he was thick to top it off. Waver placed his hand around the throbbing length, stroking the smooth, but hard flesh.

     “You’re…” Waver stammered, “Really big…”

     “Are you scared?” Iskandar asked.

     “A little…”

     “We don’t have to go all the way if you don’t want to.”

     “No, I want to… I’ve just… never had sex before…”

     Iskandar closed his eyes and smiled, “To think I’d be honored with being your first.”

     Waver looked down at the massive cock twitching in his hands and swallowed in anticipation. He lowered his head and locked his lips around it, licking the precum off of the swollen tip. As Iskandar had just taken a shower, the musky smell wasn’t near as potent as Waver expected. Iskandar ran his fingers through Waver’s long hair and grunted in delight as Waver bobbed his head up and down Iskandar’s length.

     “You’re pretty good at this,” Iskandar growled.

     Hearing that from Iskandar made Waver only want to please him more. He took a deep breath in through his nose before swallowing Iskandar’s cock to the base. The head of Iskandar’s dick rammed into his soft palate, making Waver gag. He pulled away, coughing violently with saliva and tears dripping down his face.

     “Sorry,” he said hoarsely, “I’ve never given head before.”

     Iskandar kissed him chastely, “You were great. And you needn’t feel bad. Deep throating is difficult. Now, how about I pleasure you?”

     He aligned his cock with Waver’s and gripped his hand around them, stroking them together. The combined friction of Iskandar’s hand and dick was enough to drive Waver mad with lust. Without stopping his strokes, Iskandar dove back in to kiss Waver on his soft lips, muffling Waver’s moans of pleasure. Waver ran his fingers down the firm muscles of Iskandar’s back, caressing his rough, sun-kissed skin. Suddenly, Iskandar removed his hand from their cocks and pulled away from the kiss. With this stimulation alone, Waver was already teetering on the brink of orgasm.

     “You’re really sensitive,” Iskandar purred, trailing his hand down Waver’s body to grope his soft butt, “I can only imagine how much pleasure you’ll feel here. Do you have any lube?”

     Waver turned his head embarrassedly, “In the nightstand drawer…”

     Iskandar opened the drawer to find a half full bottle of lubricant. He squirted a generous amount on his fingers before gently massaging Waver’s puckered entrance. Waver shivered as one of Iskandar’s thick fingers wriggled inside of him.

     “You’re a little tight,” Iskandar comforted, “Relax. I’ll make you feel amazing.”

     Waver inhaled deeply. He had fingered himself a few times before, but his fingers were practically bone in comparison to Iskandar’s thick digits. Suddenly a pulse of pleasure pounded in his abdomen as Iskandar swiped against his prostate. Waver whimpered in delight as Iskandar pressed harder into the sensitive gland.

     “Looks like I’ve found it,” Iskandar grinned shrewdly.

     “Sh-shut up…” Waver hissed.

     He let out a loud moan as Iskandar pressed in another finger, arching his back into the stretch. Despite the initial discomfort, Waver was starting to feel really good. Iskandar peppered kisses across Waver’s body as he slid a third finger inside. Waver’s dick twitched. With every stroke of Iskandar’s fingers, Waver felt like he could cum at any second. If he was enjoying being fingered this much, he could only imagine how good Iskandar’s dick would feel inside of him. Iskandar pulled his fingers out and kissed Waver’s lips before coating his dick in lube.

     “Are you ready?” Iskandar asked, positioning the tip of his cock at Waver’s entrance.

     “I think so,” Waver replied breathlessly.

     Slowly and gently, Iskandar began to press inside. Waver’s eyes squeezed shut. It didn’t hurt, but having such a large, foreign object press inside of him wasn’t the most comfortable sensation.

     “Kiss me,” Waver choked out.

     As soon as he felt Iskandar’s chapped lips colliding with his own, Waver’s tension began to melt away. His muscles completely relaxed, allowing Iskandar to sheath the rest of his length inside of Waver. Iskandar ran his fingers through Waver’s hair and smiled.

     “I’m all the way in,” he whispered, “Let me know if you’re ready for me to move. Your comfort comes first.”

     Waver gazed aside awkwardly, “It doesn’t really hurt, so I guess you can move whenever.”

     Iskandar hummed, slowly drawing his dick out before gently sliding it back in. Waver wrapped his arms around Iskandar, enjoying the slow, soft rocking of Iskandar’s hips against his own. Every slick motion inside sent melting warmth through Waver’s body, and whenever Iskandar’s thick member grazed his sensitive prostate he was greeted with a sudden jolt of pleasure.

     “How are you feeling?” Iskandar asked, peppering kisses along Waver’s collarbone.

     “Good…” Waver cooed, “But can you go a little rougher?”

     “I can if you want. I was just going slow because it’s you’re first time. Your body is so tender and sweet. I didn’t want to break you.”

     “But what if I want to be broken? You don’t need to hold back on me. Fuck me, Iskandar.”

   “Oh? Well if you start saying things like that, I guess I’ll just let loose. I apologize in advance if you’re sore tomorrow.”

     Before Waver could say anything else, Iskandar had lifted Waver’s leg to his chest, slamming his cock deep inside of him. Waver was unsure if he regretted his prior statement. It genuinely felt like his body was going to fall apart from the inside out, but not from pain, from intense pleasure. Waver didn’t know what was going to break first, his body or him mind. Either way, he didn’t care. Pleasure overwhelmed his capacity for rational thought and cohesive speech. His jaw went slack as saliva, curses, and screams of ecstasy poured out of it.

     Iskandar pulled his cock out of Waver’s ass, flipping him over and forcing his face down into his pillow before jamming his cock back inside. Waver didn’t even have time to catch his breath, nor did he have the strength to fight back. At this point, he was Iskandar’s playtoy, a whimpering, moaning mess at the mercy of Iskandar’s massive cock and potent libido; and he loved every second of it. Iskandar pulled at Waver’s long, brown hair, forcing his head up and making more moans leak out of his agape mouth.

     “Aww, have I broken you already?” Iskandar teased, not ceasing his relentless assault on Waver’s body.

     “Ah… FUCK. K-keep going…” Waver mewled, “I-it feelsh amazhing…”

     “You’re feeling good then? That’s good to hear,” he growled, “Your body is a spectacle Waver; such a sensitive, warm, tight ass. It’s perfect. You’re perfect.”

     Waver buried his face in the pillow, embarrassedly hiding his blush and his pleasure. Iskandar pulled out once more, flipping him over to see his flustered face, then immediately pressing back in. He wrapped his hand around Waver’s leaking, twitching dick. They were both close.

     “I want to see your beautiful face when you orgasm,” Iskandar purred.

     Waver gripped hard at the sheets, cursing and panting roughly. All of the pleasure building inside of him felt like it was ready to burst. As Iskandar pounded into his prostate, he started to match the rhythm of his thrusts with his own hips, moaning as skin slapped against skin. His insides tightened and his vision turned white as sweet release finally overtook him. Waver screamed, shooting hot, sticky cum all over his belly. Iskandar grunted, his climax following soon after, making him spill his seed deep inside of Waver’s body. He pulled his softening cock from Waver’s hole. Waver still had yet to catch his breath, drowning in the pleasure of his orgasm. His whole body had gone limp. Even with his sticky cum starting to drip off of his stomach and Iskandar’s oozing out of his hole, Waver couldn’t move a muscle.

     “Don’t worry,” Iskandar assured, “I’ll clean you up.”

     He grabbed the towel from his shower off the floor and wiped the sweat and semen from Waver’s chest and ass. Finally Waver started to recover. He rested his hand over his eyes and let out a deep sigh.

     “Fuck…” he cursed.

     “Is everything all right?” Iskandar asked.

     “It was bloody incredible, but I could use a breather…”

     Iskandar laughed heartily and kissed him gently on the lips.

     “I’m glad you enjoyed it,” he said.

     “It… feels so surreal,” Waver breathed, high on his afterglow, “Having you as my boyfriend. I feel so lucky.”

     “I feel like the lucky one. I hope everything today was to your liking.”

     “Today was perfect. I don’t want it to end…”

     “Well, unless you’re busy, I don’t have to leave immediately tomorrow morning.”

     Waver blushed as he threw his arms around Iskandar’s shoulders, pulling him in close and kissing him lovingly.

     “You can stay as long as you want,” he smiled.

     Iskandar hugged him tightly, stroking his hair and gazing into Waver’s deep, emerald eyes. He crawled into bed, cuddling up next to his lover. Waver closed his eyes, relaxing into Iskandar’s warm embrace. As he slowly drifted asleep, he thought back to what Skadi, Tamamo, and Merlin told him. To think he would become lovers with the knight in shining armor from his childhood. Fate truly does work in strange ways.

**Notes for the Chapter:**

> Thanks for reading my fic guys! I may or may not add chapters to this, because this AU is really fun to play around with!


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